Craig Newmark, the Craig in Craigslist, has been criticized for helping to bring about an extinction event for vast swaths of the journalism world, by creating a platform that sucked up the classified advertising on which it depended. More recently, he’s been a journalism savior, distributing his riches to nonprofit newsrooms and learning institutions alike. And now, thanks to a blowup at one of them, he’s discovering darker truths about journalism—ones he may have never expected, accused newspaper villain though he was. “Craig is a good guy and a self-identified nerd who hates conflict, and he has walked into this irrational, conflict-prone world,” a journalist in Newmark’s orbit told me. “He has this very earnest view about journalism, but then what he finds is that it’s a Bonfire of the Vanities, and we’re all insane egomaniacs.”

Last week, a heated fracas burst forth at the Markup, an inchoate, data-oriented technology watchdog that Newmark had partly funded with a $20 million gift. The fireworks began when founding editor in chief Julia Angwin, a highly respected investigative reporter formerly of ProPublica and The Wall Street Journal, revealed that she had been fired via e-mail by co-founder and executive director Sue Gardner, a nonprofit veteran and former executive director of the Wikimedia Foundation. In the ensuing days, the majority of the Markup’s still small newsroom resigned in protest, and the two sides waged dueling P.R. campaigns, each one knocking down the other’s version of events in the press. Angwin, who has strong support in media circles, has portrayed a clash in which she says Gardner was angling to turn the Markup into an anti-tech advocacy platform. Gardner and the publication’s third co-founder, Jeff Larson, have vehemently rejected that characterization, pinning Angwin’s termination on what they have described as “management” failings. The latest ripple materialized on Tuesday evening, when C.J.R.published a now-infamous spreadsheet in which Gardner ranked potential job candidates on criteria ranging from “understands journalism” to social “class,” “Famous?,” and “skeptical/critical about tech’s societal effects.”

The war has put Newmark in the hot seat in a way that must be highly uncomfortable for the modest and unassuming billionaire—an introvert with a passion for the simple things in life (like bird-watching), who generally tries to stay out of the spotlight, flies commercial, takes UberPools, and is more likely to be spotted eating lunch at some hole-in-the-wall joint than he is at Michael’s.

Craigslist’s classified dominance is generally seen as one of the driving forces behind the industry’s torturous decline over the past two decades, starving local publications all over the country. But in the past year, Newmark has assumed a new reputation. His foundation, Craig Newmark Philanthropies, has donated tens of millions of dollars to an array of media outlets and journalism organizations, ranging from the CUNY and Columbia j-schools, to Poynter, New York Public Radio, and local news start-up the City. “We have to do something about the bad actors,” Newmark has been known to say of his motivations, meaning that he is funding quality reporting, at least in part, as a way to counteract all of the misinformation and journalism antagonists that abound in our current era. Some view his gifts as a kind of penance, but Newmark himself doesn't subscribe to the notion that Craigslist laid waste to the news industry. There were other factors, after all, and the news companies themselves aren’t blameless. “People throw the accusation,” he toldThe New York Times in October. “I look at the facts and stick with that.”

Advertisement

Newmark’s $20 million donation to the Markup was among the largest checks he’s written, which is why the principals and the public alike are now looking at the 66-year-old erstwhile Web entrepreneur to sort out what went wrong, and how to proceed. Newmark was at the forefront of the scandal almost immediately—Angwin wrote to him after she was fired, seeking his intervention, and her letter was provided to the Times. A second letter to Newmark, from seven journalists who worked under Angwin at the Markup, was then publicized on Twitter. In short order, Newmark Philanthropies and the Markup’s five smaller-ticket backers issued a joint statement saying they are “taking steps” to “reassess” their support. Newmark has only publicly stated that he is “taking this very seriously.” As tech-journalism kingpin Walt Mossbergtweeted, “It’s an awful situation that will be a big test for the main funder, @craignewmark.” In a less charitable characterization, New Yorker staff writer Adam Davidsonimplored, “@craignewmark Make it Stop!!! You asked for time. Time’s up. Your inaction hurts now.”

After I e-mailed Newmark, a spokeswoman replied saying that he wasn’t able to speak on the record just yet. But I was able to capture the pickle he’s in through conversations with media figures who’ve interacted with him extensively. “This sort of stuff is just not at all what he is comfortable with,” one of them said. “He wasn’t investing in the nunnery. Journalism can be very rough-and-tumble, where people write stories that are tough and sometimes go after people. And I just think the very thing that makes him so good—which is that he stays out of everybody’s business—I think also maybe blinded him to what kind of world this can be.”

In today’s media landscape, where the super-rich—and tech titans, in particular—are often seen as the only viable option either for reviving struggling publications or getting new ones off the ground, there are different models of billionaire backing. There’s the Jeff Bezos and Marc Benioff playbook, in which philanthropically minded rich people come to the rescue of iconic trophy publications with the goal of transforming them into thriving businesses. And then there’s the Newmark model, in which rich people open their bank accounts purely out of the goodness of their hearts. Even within the journalistic donor class, there are funders who like to keep close tabs on what their fundees are up to—providing feedback, weighing in on coverage, asking for written reports on this or that, and so on. Newmark, according to people who have interacted with him in a donor capacity, is the polar opposite. “He was the most hands-off funder ever,” Angwin told Brian Stelter on his Reliable Sources podcast last week. “And so it makes sense that, in some ways, he was hands-off about this. . . . Craig Newmark was the perfect funder, because he isn’t in tech anymore, he was super hands-off—had no involvement in editorial, no interest in the involvement—and so that was such a great opportunity that I hope still might be salvaged.”

In addition to his generous bankrolling of news organizations, Newmark has also become a popular figure on the Manhattan media circuit. He and his wife split their time between San Francisco and New York, where they have been hosting intimate gatherings at the 19th-century Greenwich Village duplex they bought for nearly $6 million in 2016—a launch event for the City, a PEN America soirée, an Alan Rusbridger book party, etc. A couple of weeks ago, Newmark and his strategic adviser, the digital-media vet Vivian Schiller, convened a group of prominent female journalists like Lydia Polgreen and Emily Ramshaw for a salon-style shindig on the topic of women in media. Next week, Newmark is hosting a small reception following a C.J.R. symposium at Columbia, which will be his first public appearance in the aftermath of the Markup drama. In typical Newmark fashion, he tends to hunker down in a particular spot as opposed to schmoozing all over the room. “He’s just a good guy who comes in and gives you a check and goes away,” one of my sources said. “And as a result, everybody loves him, and he has these parties where everyone in New York media shows up.”

Advertisement

It’s unclear what happens next. Newmark could decide to pull funding from the Markup, which is now operating with a skeleton crew ahead of a scheduled launch in July. He could decide to divert the funds to a new publication in the same vein as the Markup, which Angwin has said she is exploring. Or he and the other backers could determine that Angwin’s firing was justified and leave everything as is. At the same time, the whole saga has sparked a conversation about whether people like Newmark wouldn’t be better off sinking their riches into deserving publications that are already tried and tested. Another start-up that Newmark had backed—to the far smaller sum of $100,000—Dutch publication the Correspondent, has recently been mired in a controversy of its own, after misrepresenting its intentions to create a “U.S.-focused” newsroom. “Here’s an idea for funders and individuals who care about journalism: support existing news organizations that are already doing great work!” Polgreen tweeted. Columbia Journalism School professor Bill Grueskinagreed: “Compare the great journalism being [done] by existing sites, newspapers and stations, vs the opaque/questionable management at places like @decorrespondent ($2.5 million) or @team_markup ($20 million est.).”

In the meantime, all that Markup and Angwin can do is wait. While there’s no word on timing from Newmark’s camp—a rep from Weber Shandwick, which works with Newmark, didn’t respond to my follow-ups—people familiar with the matter suggested to me that it would be at least another couple of weeks before anything is decided. “He’s unmistakably been the good guy,” one of my sources said, “but with this whole episode, he’s going to have to pick a side, and for the side he doesn’t pick, he’s gonna be the bad guy. That’s really uncomfortable.”